RESUMO
A mild protocol for the synthesis of diaryl and heteroaryl sulfides is described. In a one-pot procedure, thiols are converted to sulfenyl chlorides and reacted with arylzinc reagents. This method tolerates functional groups including aryl fluorides and chlorides, ketones, as well as N-heterocycles including pyrimidines, imidazoles, tetrazoles, and oxadiazoles. Two compounds synthesized by this method exhibited selective activity against the MCF-7 breast cancer cell line in the micromolar range.
Assuntos
Antineoplásicos/síntese química , Cloretos/química , Imidazóis/química , Cetonas/química , Células MCF-7/química , Células MCF-7/efeitos dos fármacos , Ácidos Sulfênicos/síntese química , Compostos de Sulfidrila/química , Sulfetos/síntese química , Antineoplásicos/química , Catálise , Humanos , Estrutura Molecular , Sulfetos/químicaRESUMO
Alkyl Grignard reagents that contain ß-hydrogen atoms were used in a stereospecific nickel-catalyzed cross-coupling reaction to form C(sp(3))-C(sp(3)) bonds. Aryl Grignard reagents were also utilized to synthesize 1,1-diarylalkanes. Several compounds synthesized by this method exhibited selective inhibition of proliferation of MCF-7 breast cancer cells.
Assuntos
Alcanos/síntese química , Alcanos/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Neoplasias da Mama/tratamento farmacológico , Níquel/química , Alcanos/química , Antineoplásicos/química , Catálise , Linhagem Celular Tumoral , Feminino , Humanos , Hidrocarbonetos Aromáticos/síntese química , Hidrocarbonetos Aromáticos/química , Hidrocarbonetos Aromáticos/farmacologia , Indicadores e Reagentes , EstereoisomerismoRESUMO
Stereospecific nickel-catalyzed cross-coupling reactions of benzylic 2-methoxyethyl ethers are reported for the preparation of enantioenriched 1,1-diarylethanes. The 2-methoxyethyl ether serves as a traceless directing group that accelerates cross-coupling. Chelation of magnesium ions is proposed to activate the benzylic C-O bond for oxidative addition.
